Oxidative aliphatic carbon-carbon (C-C) bond cleavage reactions mediated by first-row transition metals and involving O2 as the terminal oxidant are important for synthetic and industrial applications. Chemistry involving the oxidative cleavage of diketones is particularly of interest as these molecules can serve as a source for valuable small molecules such as carboxylic acids and benzil. To date, there is little mechanistic information available for diketone cleavage reactions involving O2. To gain insight into the O2 reactivity of first row metal diketonates, our laboratory has pursued substituted diketonate derivatives that exhibit reactivity with O2 at ambient temperature. In a portion of this chemistry, we have pursued studies of light-induced reactivity of Ni(II)-coordinated chlorodiketonates and the thermal reactivity of Cu(II) chlorodiketonates in the presence of O2. The results of these studies can be compared to the light-induced reactivity of non-coordinated chlorodiketones, which has been previously reported. In the research to be presented, we have further examined how the metal and its supporting chelate ligand environment influence the O2 reactivity of a chlorodiketonate ligand. Specifically, using bipyridine-ligated Co(II) complexes, we have examined light-induced O2-dependent aliphatic C-C bond cleavage processes. Our results demonstrate that the product mixture is highly sensitive to the nature of the supporting metal/ligand environment.

Photoinduced O2-dependent aliphatic C-C bond cleavage using a bipyridine-ligated Co(II) complex

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.